Introduction to "The Game"

My name is TIL.  I'm a miles and points addict.

I suppose I've been involved since I was a child, and my parents opened up United frequent flyer accounts for my sister and me.  We weren't old enough to understand the meaning of the points, but we knew one day we might be able to earn a free trip.

Fast forward to college, and I started picking up a couple of points-earning credit cards.  The Chase United Visa came first, followed by the original Amtrak card.  I'm freakishly tall and don't fit in economy class seats, so I always had a goal of going to Australia or New Zealand in business class on saved up United miles, but United always seemed to raise the threshold just as I got close to reaching it.    I continued to fly United whenever I had the chance, saving up a few hundred more miles with each trip.  The Amtrak card paid off a lot quicker, since it provided dollars toward Amtrak tickets instead of points, and I could earn cool things like a bedroom on the Auto Train for free.

It wasn't until my girlfriend moved to California that I really started to see the value in playing the miles and points game.  At the time, I was living in Michigan.  Northwest Airlines was running specials where you could fly from Grand Rapids to San Francisco for $240 all-in, and Mrs. TIL and I took full advantage of the deal.  Each direction, we would rack up another 2500 WorldPerks miles, and we quickly obtained Silver Elite status, almost without knowing it.  Suddenly, we were getting upgraded to first class on almost every flight, and racking up even more miles and free trips.

While in California, we also discovered Priceline, and started booking weekends in wine country based based on online user reports of other wins.  I remember staying at a 5 star independent boutique hotel for $40, with breakfast, right in the middle of wine country.  Incredible!

For two young adults living on a fixed budget and doing a lot of post-9/11 flying, getting free first class upgrades and paying almost  nothing for really nice hotels was a big deal, and we started to realize that the more we "played the game", the more the hotels and airlines would send us more promotions, give us more perks, and encourage us to play the game even more.

Fast forward a few more years, and I've come to the realization that this game is much less about fancy hotels and first class seats, and more about opportunities to visit some of the most incredible places in the world.  I hope this blog will help others understand the incredible opportunities this gave can open up to almost any American with a decent credit score and a few hours of planning.

Over the years, I've learned many things about the miles and points game, and I'd like to finish out my first post with a few thoughts on the game as a whole:

• Signing up for credit cards and taking advantage of travel promotions is like playing at a casino where you always win.  Any perceived downside potential is quickly erased when you realize you're being rewarded for playing the game.  In other words, signing up for a new credit card to get 100,000 free frequent flyer miles is perceived to be risky because it puts a mark on your credit report.  However, the sign-up will invariably increase your credit line and build your credit history, ultimately raising your score and encouraging banks to provide additional sign-up opportunities.
• Paying for flights is not the best way to earn frequent flyer miles.  Fifteen years of collecting United miles for flights and spending on a United credit card resulted in a stash of 90,000 miles, while signing up for a new pair of American Airlines credit cards resulted in 150,000 miles overnight.  As long as there are more lucrative ways to collect miles, paying for flights to get frequent flyer miles is a waste of money.
• By playing this game, we've been able to go places and experience things far beyond what we ever could done if we weren't playing the game.  We've traveled places where few Americans have ever set foot.  We've experienced cultures and value systems that are so vastly different from the American way of live that they're almost incomprehensible.  We've stayed in hotels alongside the richest people in the world, and walked beside some of the poorest.  We've seen the problems our world faces first-hand, but also experienced the unexpected kindness of strangers.  This game is about much more than getting good deals on travel -- it's about understanding our very small place in a very big world.